US7910018B2ExpiredUtilityPatentIndex 35
Compounds for use in liquid crystal devices
Est. expiryNov 3, 2024(expired)· nominal 20-yr term from priority
C09K 2323/03C09K 2323/00C09K 2019/3425C09K 19/3402C07D 319/08
35
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Cited by
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References
32
Claims
Abstract
Liquid crystal compounds of Formula (I) for use in liquid crystal devices contains a dioxatetralin unit within the mesogenic liquid crystal core. The dioxatetralin unit may be located at any position within the mesogenic core of the liquid crystal compound, either at the terminus of the liquid crystal core or alternatively substantially in the middle of the liquid crystal core. The compounds of the invention exhibit fast switching and may be used in liquid crystal mixtures for particular use in imaging or display media, such as monitors or televisions.
Claims
exact text as granted — not AI-modified1. A compound of Formula (I)
wherein R 1 and R 2 are independently selected from cyano, halo, optionally substituted hydrocarbyl, optionally substituted alkoxy, optionally substituted heterocyclyl, a group R 13 C(O)O— or R 13 OC(O)— where R 13 is optionally substituted hydrocarbyl;
R 3 , R 4 and R 5 are independently selected from hydrogen, halogen, CF 3 or SF 5 ;
X 1 , X 2 , X 3 and X 4 are independently selected from a direct bond, —CH 2 CH 2 —, —(CH 2 ) 4 —, —CH 2 O—, —CH═CH—, —C≡C—, —COO—,
—OCO—, or —OCH 2 —;
and A, B, C and D are independently selected from a 1,4-phenylene, 1,4-cyclohexyl or a heterocyclic ring, any of which may be optionally substituted provided that at least one of rings C or D must be present;
and n is 0 or 1, m is 0 or 1, p is 0 or 1 and k is 0 or 1, provided that k+m+n+p is greater than 0, further provided that if k is 0 then n is 0, and also provided that if m is 0 then p is 0.
2. A compound according to claim 1 wherein both R 1 and R 2 are independently selected from alkyl or alkoxy.
3. A compound according to claim 2 wherein the alkyl or alkoxy groups have from 3 to 8 carbon atoms.
4. A compound according to claim 1 wherein R 3 , R 4 and R 5 are selected from hydrogen or fluorine.
5. A compound according to claim 1 wherein X 1 , X 2 , X 3 and X 4 are selected from a direct bond or a group —CH 2 CH 2 —.
6. A compound according to claim 5 wherein X 1 , X 2 , X 3 and X 4 are direct bonds.
7. A compound according to claim 1 where k+m+n+p is 1 or 2.
8. A compound according to claim 1 wherein, when present each of rings A, B, C or D is substituted by at least one fluorine atom.
9. A compound according to claim 8 wherein there are 2 or more fluorine atoms present.
10. A compound according to claim 1 wherein A, B, C and D are selected from 1,4-phenylene, 1,4-cyclohexyl, 2,5-dioxanyl, pyridyl or 2,5-pyrimidinyl.
11. A compound according to claim 10 wherein A, B, C and D are selected from 1,4-phenylene or 1,4-cyclohexyl.
12. A compound according to claim 1 , comprising a compound of Formula (XX)
where R 1 , R 2 , R 3 , R 4 , R 5 , X 1 , X 3 , A and C are as defined in claim 1 .
13. A compound according to claim 12 wherein each of rings A and C are substituted by at least one fluorine atom.
14. A compound according to claim 12 wherein there are 2 or more fluorine atoms present.
15. A compound according to claim 12 , comprising a compound of Formula (XV)
where R 1 , R 2 , R 3 , R 4 , R 5 , X 3 and X 1 are as defined in claim 12 , R 14 and R 15 are independently selected from hydrogen or halogen.
16. A compound according to claim 15 wherein one, two or three of R 3 , R 4 , R 5 , R 14 and R 15 are fluorine and the others are hydrogen.
17. A compound according to claim 12 , comprising a compound of Formula (XXV)
where R 1 , R 2 , R 3 , R 4 , R 5 , X 1 and X 3 are as defined in claim 12 , and R 14 , R 15 , R 44 and R 45 independently selected from hydrogen or halogen.
18. A compound according to claim 17 wherein one, two or three of R 3 , R 4 , R 5 , R 14 and R 15 are fluorine and the others are hydrogen.
19. A compound according to claim 1 , comprising a compound of Formula (XVIII)
where p, m, R 1 , R 2 , R 3 , R 4 , R 5 , X 3 , X 4 , C and D are as defined in claim 1 .
20. A compound according to claim 19 wherein rings C or D are substituted by at least one fluorine atom.
21. A compound according to claim 20 wherein there are 2 or more fluorine atoms present.
22. A compound according to claim 19 , comprising a compound of Formula (XXX)
where R 1 , R 2 , R 3 , R 4 , R 5 , and X 3 are as defined in claim 19 , and R 44 and R 45 are independently selected from hydrogen or halogen.
23. A compound according to claim 22 wherein one, two or three of R 3 , R 4 , R 5 , R 44 and R 45 are fluorine and the others are hydrogen.
24. A compound according to claim 19 , comprising a compound of Formula (XXXV)
where R 1 , R 2 , R 3 , R 4 , R 5 , X 3 and X 4 are as defined in claim 19 , and R 44 , R 45 , R 46 and R 47 are independently selected from hydrogen or halogen.
25. A compound according to claim 24 wherein one, two or three of R 3 , R 4 , R 5 , R 44 , R 45 , R 46 and R 47 are fluorine and the others are hydrogen.
26. A liquid crystal mixture comprising at least one compound according to claim 1 .
27. A liquid crystal device comprising at least one compound according to claim 1 .
28. A liquid crystal device comprising a liquid crystal mixture according to claim 26 .
29. A device comprising two spaced cell walls each bearing electrode structures and treated on at least one facing surface with an alignment layer, a layer of a liquid crystal material enclosed between the cell walls, characterised in that it comprises at least one compound of claim 1 .
30. A liquid crystal device according to claim 27 , wherein the device is an Active Matrix Device, an STN device or a TN device.
31. A device according to claim 27 , wherein the cell walls comprise at least 4 electrodes such as to allow said liquid crystal compound or mixture to be switched in at least two directions.
32. A method of preparing a device comprising at least one liquid crystal compound according to claim 1 .Cited by (0)
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